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As an art teacher with basic industrial arts training, Kilpin likely found it difficult to gain recognition within the crowded British ‘fine arts’ world. His well connected brother George, who was Vice-President and General Manager of Imperial Oil in Montreal, encouraged him to move and offered help to get him established.

Kilpin’s English background would carry substantial cachet in English Canada of this period, where the main arts organizations and educational programs were based on British models. He was soon teaching at the Montreal Technical Institute and then in public schools in the Westmount School District. In 1907, he became a member of the Art Association of Montreal (AAM), the country’s largest, most distinguished private arts organization and the domain of prominent art collectors and patrons.
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